Nghiên cứu tổng hợp các hybrid mới của artemisinin với zidovudin (AZT)

Lê Huy Bình, Vũ Đình Tiến, Hoàng Xuân Tiến, Trần Khắc Vũ


The synthesis of new hybrids of artemisinin with zidovudin (AZT) was described via six-step procedure. Firstly, the reaction of dihydroartemisinin (2) with NaN3 in the presence of (CH3)3SiCl and a catalytic amount of KI in CH2Cl2 at ice water temperature gave 10β-azidoartemisinin (4). This compound was then hydrolysed by Ph3P in THF/H2O at 65 oC for 6 h to furnish 10β-azidoartemisinin (5). Next, the reaction of 5 with anhydride dicacboxylics (anhydride glutaric, 3,3-dimethyl anhydride glutaric) in the presence of DMAP gave new intermediates 7a,b. Compound 6 was obtained by the reaction of 5 with suberic acid monomethyl ester in CH2Cl2 in the presence of EDC and DMAP at ambient temperature, followed by the hydrolysis in CH2Cl2/EtOH = 9:1 using NaOH 0.2 N. Finally, the reaction of 6 and 7a,b with AZT in CH2Cl2 using EDC and DMAP as a catalytic system afforded novel hybrids 8a-c in moderate yields. The structures of synthesized compounds were confirmed based on spectroscopic methods: IR, NMR and HRMS.

Keywords. Artemisinin, dihydroartemisinin, artemether, arteether, sodium azide, hybrid.


Artemisinin, dihydroartemisinin, artemether, arteether, sodium azide, hybrid

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